Hockey Tips for Entrepreneurs: Do You Know Where the Puck is Going?

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While not a huge hockey fan, I am a great
admirer of the sport’s legend Wayne Gretsky. I simply am in
awe when women and men come around in any field and dominate their
craft; as an ever-curious entrepreneur I am fascinated by how they
view the world.

I read recently that when Gretsky was asked what he thought
about when he was on the ice, he paused a long moment and
said: “I’m always thinking about where the puck is going, not
where it is.”

This blew me away. It is really so simple, so obvious at a
level. But when one is working twenty hours on the day-to-day
mission at hand, how much stands in our way – or we let stand in
our way – to think where the pucks we chase will be?

When my team and I first started HealthCentral, the social and
content platform for people to learn and share their health and
wellness experiences, one of the all-time great Silicon Valley
entrepreneurs – a Gretsky of his field for sure – emailed me to
say:

“Congratulations! Welcome to our world where there are two
and only two emotions: utter euphoria and abject fear!” I
knew what he meant by the end of the first week.

The euphoria is easy to describe – on certain days you believe
with every ounce of your being that you are building that which was
never been there before. Even the abject fear part is pretty
easy. In one of our start-ups we must have had in the first
two years alone three near-bankruptcy moments. I can tell you
that in my venture investing I have seen more investments than my
wife would allow me to admit go crashing to zero.
Failure or risk of failure – an acceptance that it is
the norm in these ever changing technological worlds and, while it
stinks, one must simply dust themselves off, learn, and get back at
it – is at the essence of entrepreneurship.

But my friend wasn’t just talking about fear of failure in
binary terms, but also the daily discomfort with uncertainty that
can blind us from looking up and watching where the puck is
moving. Some of us, but much less than one would guess in my
experience, really thrive in daily uncertainty. The best of
us want to innovate, we want to solve interesting problems, we want
to have our opinion matter, and we assuredly want
independence. But we often want to be told what to do and/or
seek comfort in creating a tried and true “way things are
done.”

With this comes two of the most corrupting forces in a fast
growing innovation organization: first, a view that we are so
smart that the way we do things are the only way; second, and a
close sibling, a rising view that “we’ve always done it that
way.” There is almost defensiveness in these forces – that
somehow challenging existing, even recently developed, paradigms is
almost disloyalty.

This, of course, is compounded when a company gets to
scale. Pick your favorite example of the once unstoppable
innovation juggernauts like Kodak, Nokia, Sony all taken on if not
defeated by people who focused not on where and how they skated,
but where the puck was going.

In fact, the bigger one gets, the more one risks looking down at
their own skates. I can think of only two companies who
looked hard at the way they did things and changed 180 degrees.
IBM once had over 70% of their revenue tied to mainframe
computing, clearly to puck-watchers destined to be overwhelmed
by personal computing and in less than two years they
effectively exited it. Intel, who had made its name and a
multi-billion dollar business in the commodity chip business
similarly simply decided to get into more complicated
processors.

One of my favorite stories from the latter was how Intel founder
Andy Grove did something I’ve recreated 100 times since even in my
early stage enterprises. He and his co-founder turned to each
other and said, “Let’s go into the other room and come back and
pretend we were our own board of directors. What would we
do?” It was a short meeting. They knew the answer –
leave the commodity chip business. But it took this simple
framework to help them see the puck they only sensed was moving
away for them for years.

In the world of start-ups if I’ve seen anything utterly
consistent among the greatest world-class teams it is three
things:

Complete, company-wide belief in, understanding of,
and passion for the mission at all levels.
Companies in Silicon Valley and New York City have drawn
criticism for placing making money too hight in the last of
priorities of late. I can’t, however, think of one that
succeeded based on passion and vision alone (and I can name a few
famous ones struggling mightily because of it). In fact,
without a doubt, those who did achieve financial success did so as
an outgrowth of passion and execution for their mission.

It sounds like a cliché, but people are
everything. It takes very few naysayers
and doubters to be real cancers in an organization. But the
culture, starting with leadership, can inoculate here from the
beginning if consistently applied in the years that follow.
Tony Hsieh of Zappos fame is a
Gretsky in entrepreneurship across more than one sport and I love
the policy he and his team adopted: paying people to leave their
company. If for a few thousand bucks you’d leave, you were
never in to begin with, and you were more than likely to be one of
those cultural cancers.

Tony is rare – and few seem willing to go this far. But world
class organizations have people: knowing and utterly committed to
the mission; knowing how they fit in the mission and can impact it;
knowing how one can grow in their career and skills; encouraging
acceptance of failing and flexibility of pivoting to new realities;
inspiring curiosity in all things; displaying in action genuine
team work – not lip service. In one of my favorite portfolio
companies today no one –regardless of function – goes home until
they check on their fellow colleagues.

Finally, they really look and reward what Peter
Thiel and one of his colleagues Auren Hoffman calls “unobvious
connections.” Great companies understand what
needs to be executed today, but they keep looking up – push each
other to keep looking up for the big picture of change. They
ask themselves and execute on what could be. They are the
customers and consumers that they seek – today, and where the puck
of unlimited and ubiquitous technological innovation can take
them.